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WO2002046329A1 - Milieu a cristaux liquides - Google Patents

Milieu a cristaux liquides Download PDF

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Publication number
WO2002046329A1
WO2002046329A1 PCT/EP2001/010901 EP0110901W WO0246329A1 WO 2002046329 A1 WO2002046329 A1 WO 2002046329A1 EP 0110901 W EP0110901 W EP 0110901W WO 0246329 A1 WO0246329 A1 WO 0246329A1
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WO
WIPO (PCT)
Prior art keywords
compounds
medium according
ocf
formula
alkyl
Prior art date
Application number
PCT/EP2001/010901
Other languages
German (de)
English (en)
Inventor
Michael Heckmeier
Brigitte Schuler
Achim GÖTZ
Peter Kirsch
Detlef Pauluth
Matthias Bremer
Sabine Schoen
Georg LÜSSEM
Christian Hock
Original Assignee
Merck Patent Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE2000160744 external-priority patent/DE10060744B4/de
Priority claimed from DE2001125706 external-priority patent/DE10125706A1/de
Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh
Priority to US10/433,002 priority Critical patent/US7078079B2/en
Priority to AU2001289901A priority patent/AU2001289901A1/en
Publication of WO2002046329A1 publication Critical patent/WO2002046329A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition

Definitions

  • the present invention relates to a liquid-crystalline medium, its use for electro-optical purposes and displays containing this medium.
  • Liquid crystals are mainly used as dielectrics in display devices, since the optical properties of such substances can be influenced by an applied voltage.
  • Electro-optical devices based on liquid crystals are well known to the person skilled in the art and can be based on various effects. Such devices are, for example, cells with dynamic scattering, DAP cells (deformation of aligned phases), guest / host cells, TN cells with a twisted nematic ("twisted nematic”) structure, STN cells (“super-twisted nematic”), SBE cells (“superbirefringence effect”) and OMI cells (“optical mode interference”).
  • the most common display devices are based on the Schadt-Helfrich effect and have a twisted nematic structure.
  • the liquid crystal materials must have good chemical and thermal stability and good stability against electric fields and electromagnetic radiation. Furthermore, the liquid crystal materials should have a low viscosity and result in short response times, low threshold voltages and a high contrast in the cells.
  • nematic or cholesteric mesophase for the above-mentioned cells.
  • liquid crystals are generally used as mixtures of several components, it is important that the components are readily miscible with one another.
  • media with large positive dielectric anisotropy, wide nematic phases, relatively low birefringence, very high resistivity, good UV and temperature stability and low vapor pressure are desired for matrix liquid crystal displays with integrated non-linear elements for switching individual pixels (MLC displays).
  • Such matrix liquid crystal displays are known.
  • active elements i.e. transistors
  • non-linear elements for the individual switching of the individual pixels.
  • active matrix whereby one can distinguish two types:
  • MOS Metal Oxide Semiconductor
  • TFT Thin film transistors
  • the TN effect is usually used as the electro-optical effect.
  • TFTs made from compound semiconductors such as CdSe or TFTs based on polycrystalline or amorphous silicon.
  • the TFT matrix is applied to the inside of one glass plate of the display, while the other glass plate carries the transparent counter electrode on the inside.
  • the TFT is very small and practically does not disturb the image.
  • This technology can also be expanded for fully color-compatible image representations, with a mosaic of red, green and blue filters being arranged in such a way that one filter element each is opposite a switchable image element.
  • the TFT displays usually work as TN cells with crossed polarizers in transmission and are illuminated from behind.
  • MLC displays of this type are particularly suitable for TV applications (e.g. pocket TVs) or for high-information displays for computer applications (laptops) and in automobile or aircraft construction.
  • TV applications e.g. pocket TVs
  • high-information displays for computer applications (laptops) and in automobile or aircraft construction.
  • difficulties arise with MLC displays due to the insufficiently high specific resistance of the liquid crystal mixtures [TOGASHI, S., SEKIGUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K. , TAJIMA, E., WATANABE, H., SHIMIZU, H., Proc. Eurodisplay 84, Sept. 1984: A 210-288 Matrix LCD Controlled by Double
  • the invention has for its object to provide media in particular for such MFK, TN or STN displays, which do not have the disadvantages indicated above or only to a lesser extent, and preferably at the same time have very high resistivities and low threshold voltages.
  • the mixtures according to the invention are particularly suitable for low ⁇ n applications.
  • the mixtures according to the invention are preferably used in reflective and transflective applications.
  • the invention thus relates to a liquid-crystalline medium based on a mixture of polar compounds with positive or negative dielectric anisotropy, characterized in that it contains one or more compounds of the general formula I
  • -CO-, -CO-O-, -O-CO- or -O-CO-O- can be replaced so that O atoms are not directly linked
  • Z 1 and Z 2 each independently of one another —CF 2 CF 2 - or a single bond, where Z 1 ⁇ Z 2 ,
  • the compounds of formula I have a wide range of uses. Depending on the choice of the substituents, these compounds can serve as base materials from which liquid-crystalline media are predominantly composed; but it can compounds of the formula I, liquid-crystalline base materials from other classes of compounds, can be added, for example, to influence the dielectric and / or optical anisotropy of such a dielectric and / or to optimize its threshold voltage and / or its viscosity.
  • the compounds of the formula I are colorless in the pure state and form liquid-crystalline mesophases in a temperature range which is favorable for electro-optical use. They are stable chemically, thermally and against light.
  • R 1 is an alkyl radical and / or an alkoxy radical, this can be straight-chain or branched. It is preferably straight-chain, has 2, 3, 4, 5, 6 or 7 carbon atoms and accordingly preferably means ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexoxy or heptoxy, furthermore methyl , Octyl, nonyl, decyl, undecyl, dodecyl, methoxy, octoxy, nonoxy, decoxy or undecoxy.
  • R 1 is an alkyl radical in which one CH 2 group has been replaced by -O- and one has been replaced by -CO-, these are preferably adjacent. Thus, they include an acyloxy group -CO-O- or an oxycarbonyl group -0-CO-. These are preferably straight-chain and have 2 to 6 carbon atoms.
  • R 1 is an alkyl or alkenyl radical which is simply substituted by CN or CF 3 , this radical is preferably straight-chain. The substitution by CN or CF 3 is in any position.
  • R is an alkyl or alkenyl radical which is at least monosubstituted by halogen
  • this radical is preferably straight-chain and halogen is preferably F or Cl.
  • halogen is preferably F.
  • the resulting residues also include perfluorinated residues.
  • the fluorine or chlorine substituent can be in any position, but preferably in the ⁇ position.
  • Compounds of the formula I which have wing groups R 1 suitable for polymerization reactions are suitable for the preparation of liquid-crystalline polymers.
  • Branched groups of this type usually contain no more than one chain branch.
  • Isopentyl 3-methylbutyl
  • 2-methylpentyl 3-methylpentyl
  • 2-ethylhexyl 2-propylpentyl
  • isopropoxy 2-methylpropoxy, 2-methylbutoxy, 3-methylbutoxy
  • 2-methylpentoxy 3-methylpentoxy
  • 2- Ethylhexoxy 1-methylhexoxy, 1-methylheptoxy.
  • Ri represents an alkyl radical in which two or more CH 2 groups have been replaced by -O- and / or -CO-O-, this can be straight-chain or branched. It is preferably branched and has 3 to 12 carbon atoms. Accordingly, it means especially bis-carboxy-methyl, 2,2-bis-carboxy-ethyl, 3,3-bis-carboxy-propyl, 4,4-bis-carboxy-butyl, 5,5-bis-carboxy-pentyl, 6,6-bis-carboxy-hexyl, 7,7-bis-carboxy-heptyl, 8,8-bis-carboxy-octyl, 9,9-bis-carboxy-nonyl, 10,10-bis-carboxy-decyl, Bis (methoxycarbonyl) methyl, 2,2-bis (methoxycarbonyl) ethyl, 3,3-bis (methoxycarbonyl) propyl, 4,4-bis (methoxycarbon
  • the invention also relates to electro-optical displays (in particular STN or MFK displays with two plane-parallel carrier plates which form a cell with a border, integrated non-linear elements for switching individual pixels on the carrier plates and a nematic liquid crystal mixture in the cell with a positive one dielectric anisotropy and high resistivity) containing such media and the use of these media for electro-optical purposes.
  • electro-optical displays in particular STN or MFK displays with two plane-parallel carrier plates which form a cell with a border, integrated non-linear elements for switching individual pixels on the carrier plates and a nematic liquid crystal mixture in the cell with a positive one dielectric anisotropy and high resistivity
  • the mixtures according to the invention are also suitable for IPS applications (in plane switching), OCB applications (optically controlled birefringence) and VA applications (vertical alignment).
  • liquid crystal mixtures according to the invention allow a significant expansion of the available parameter space.
  • STN and MKF ads can be achieved.
  • the mixtures are characterized by small operating voltages.
  • the TN thresholds are below 2.0 V, preferably below 1.8 V, particularly preferably ⁇ 1.7 V.
  • the MFK displays according to the invention preferably operate in the first transmission minimum according to Gooch and Tarry [OH. Gooch and H.A. Tarry, electron. Lett. 10, 2-4, 1974; CH. Gooch and H.A. Tarry, Appl. Phys., Vol. 8, 1575-1584, 1975], where in addition to particularly favorable electro-optical properties such as e.g.
  • the flow viscosity v 2 o at 20 ° C. is preferably ⁇ 60 mm 2 -s "1 , particularly preferably ⁇ 50 mm 2 -s " 1 .
  • the rotational viscosity . the mixtures according to the invention at 20 ° C. is preferably ⁇ 180 mPa-s, particularly preferred ⁇ 150 mPa s.
  • the nematic phase range is preferably at least 90 °, in particular at least 100 °. This range preferably extends at least from -20 ° to + 80 °.
  • the UV stability of the mixtures according to the invention is also considerably better. H. they show a significantly smaller decrease in HR under UV exposure.
  • the media according to the invention are preferably based on several (preferably two or more) compounds of the formula I, i.e. the proportion of these compounds is 5-95%, preferably 10-60% and particularly preferably in the range of 15-50%.
  • X preferably denotes F, Cl, CN, OCN, NCS, SCN, SF 5 , OCH 3 , CH 3 , OC 2 H 5> C 2 H 5 , OC 3 H 7> C 3 H 7> CF 3 , CF 2 H , OCF 3, OCF 2 H, OCFHCF 3> OCFHCH 2 F, OCFHC 2 HF, OCF 2 CH 3j OCF 2 CH 2 F, OCF 2 CHF 2, OCFsCFsCFsH, OCF 2 CF 2 CH 2 F, OCFHCF 2 CF 3l OCFHCF 2 CHF 2 , OCFHCFHCF3, OCH 2 CF 2 CF 3j OCF 2 CF2CF3, OCF 2 CFHCHF 2 , OCF 2 CH 2 CHF 2) OCFHCF 2 CHF 2) OCFHCF 2 CHF 2) OCFHCFHCHF 2 ,
  • OCFHCH 2 CF 3 OCH 2 CFHCF3, OCH2CF 2 CHF 2j OCF 2 CFHCH3, OCF2CH 2 CHF 2l OCFHCF 2 CH 3) OCFHCFHCHF 2, OCFHCH 2 CF 3, OCH 2 CF 2 CHF 2, OCH2CFHCHF2, OCF2CH2CH3, OCFHCFHCH3, OCFHCH 2 CHF 2, OCH 2 CF 2 CH3, OCH2CFHCHF2, OCHgCH ⁇ CHFg, OCHCH2CH3, OCH 2 CFHCH 3> OCH 2 CH 2 CHF 2 , OCCIFCF3,
  • OCCIFCCIF 2 OCCIFCCIF 2> OCFHCCI ⁇ F, OCCIFCHF 2, OCCIFCCIF2, OCF 2 CHCI 2> OCF2CHCI 2, OCF 2 CCI2F, OCF2CCIFH, OCF2CCIF2, OCF 2 CF 2 CCIF 2, OCF 2 CF 2 CCI 2 F, OCCIFCF 2 CF 3 > OCCIFCF 2 CHF 2 , OCCIFCF 2 CCIF 2 , OCCIFCFHCF3, OCCIFCCIFCF3, OCCI2CF2CF3, OCCIHCF 2 CF 3 , OCCIFCF 2 CF 3 , OCCIFCCIFCF3, OCF 2 CCIFCHF 2 ,
  • Ro n-alkyl, oxaalkyl, fluoroalkyl or alkenyl, each with up to
  • X ° F, Cl, halogenated alkyl, alkenyl or alkoxy with 1 to 6
  • the medium additionally contains one or more dioxanes of the formulas D1 to D4,
  • the medium additionally contains one or more compounds selected from the group consisting of the general formulas IX to XVIII:
  • Ro, ⁇ o, ⁇ and Y ⁇ each independently have one of the meanings given in claim 2.
  • X ° F preferably denotes Cl, CF 3 , OCF 3 , OCHF 2 .
  • Ro is preferably alkyl, oxaalkyl, fluoroalkyl or alkenyl, each with up to 6 carbon atoms.
  • the medium additionally contains one or more compounds with fused rings of the formulas A-1 to A-6
  • the proportion of the compounds of the formulas A-1 to A-6 is 0-20% by weight, preferably 3-15% by weight, in particular 3-10% by weight.
  • the proportion of compounds of the formulas I to VIII together is at least 30% by weight, preferably at least 50% by weight, in the mixture as a whole;
  • the proportion of compounds of the formula I in the total mixture is 1 to 50% by weight, preferably 2-30% by weight and in particular 5-25% by weight;
  • the proportion of compounds of the formulas II to VIII in the total mixture is 20 to 80% by weight;
  • the medium contains one or more compounds of the formulas II, IM, IV, V, VI, VII or VIII;
  • Ro is straight-chain alkyl or alkenyl with 2 to 7 C atoms
  • the medium consists essentially of compounds of the formulas I to VIII;
  • the medium preferably contains one, two or three compounds of the formula I;
  • the medium contains a mixture of compounds of the formula I in which Ri denotes methyl, ethyl, nC 3 H 7 , nC 4 H 9 , n-CsH ⁇ or nC 6 Hn;
  • the medium contains further compounds, preferably selected from the following group consisting of the general formulas XIX to XXII:
  • R, X, Y 1 , Y 2 and Y 3 have the meaning given above and the 1, 4-phenylene rings can be substituted by methyl, CN, chlorine or fluorine.
  • the 1,4-phenylene rings are preferably substituted one or more times by fluorine atoms.
  • the medium preferably contains carbocyclic dinuclear.
  • R ° have the meanings given for R °
  • Alkyl is a straight-chain alkyl radical with 1-8 C atoms, in particular with 2-5 C atoms.
  • the medium preferably contains two or three compounds of the formulas XXIII.
  • the proportion of the compounds of the formula XXIII in the medium according to the invention is 5-40% by weight, in particular 5-35% by weight.
  • the weight ratio I: (II + III + IV + V + VI + VII + VIII) is preferably 1:10 to 10: 1.
  • the medium essentially consists of compounds selected from the group consisting of the general formulas I to XVIII.
  • alkyl encompasses straight-chain and branched alkyl groups with 1-7 carbon atoms, in particular the straight-chain groups methyl, ethyl, propyl, butyl, pentyl, hexyl and heptyl. Groups with 2-5 carbon atoms are generally preferred.
  • alkenyl encompasses straight-chain and branched alkenyl groups with 2-7 carbon atoms, in particular the straight-chain groups.
  • Alkenyl groups in particular are C 2 .C 7 -1 E-alkenyl, C 4 -C 7 -3E-alkenyl, C 5 -C 7 -4-alkenyl, C 6 -C 7 -5-alkenyl and C 7 -6-alkenyl , in particular C 2 -C 7 -1 E-alkenyl, C 4 -C 7 -3E-alkenyl and C 5 -C 7 -4-alkenyl.
  • alkenyl groups are vinyl, 1 E-propenyl, 1 E-butenyl, 1 E-pentenyl, 1 E-hexenyl, 1 E-heptenyl, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 3E-heptenyl, 4-pentenyl , 4Z-hexenyl, 4E-hexenyI, 4Z-heptenyl, 5-hexenyI, 6-heptenyl and the like. Groups of up to 5 carbon atoms are generally preferred.
  • fluoroalkyl preferably encompasses straight-chain groups with terminal fluorine, ie fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl and 7-fluoroheptyl. However, other positions of the fluorine are not excluded.
  • oxaalkyl preferably encompasses straight-chain residues of the
  • n H 2 n + ⁇ -O- (CH 2 ) m wherein n and m each independently represent 1 to 6.
  • Mixtures which, in addition to one or more compounds of the formula I, contain one or more compounds of the formula IV, in particular compounds of the formula IVa and / or IVd, in which X ° is F, OCHF 2 or OCF 3 , are preferred.
  • the compounds of the formulas I to VIII are colorless, stable and readily miscible with one another and with other liquid crystal materials.
  • the mixtures according to the invention are distinguished by very high clearing points, the values for the rotational viscosity y . are comparatively low.
  • the response times, the threshold voltage, the steepness of the transmission characteristics, etc. can be modified as desired by suitable choice of the meanings of Ro and Xo.
  • 1 E-alkenyl residues, 3E-alkenyl residues, 2E-alkenyloxy residues and the like generally lead to shorter response times, improved nematic tendencies and a higher ratio of the elastic constants k 33 (bend) and kn (splay) compared to alkyl or alkoxy residues.
  • 4-alkenyl residues, 3-alkenyl residues and the like generally give lower threshold voltages and smaller values of k 33 / k- ⁇ compared to alkyl and alkoxy residues.
  • a -CH 2 CH 2 group generally leads to higher values of k 33 / k_ _ compared to a simple covalent bond.
  • Higher values of I kii enable, for example, flatter transmission characteristics in TN cells with 90 ° twist (to achieve gray tones) and steeper transmission characteristics in STN, SBE and OMI cells (higher multiplexability) and vice versa.
  • the total amount of compounds of the formulas I to XVIII in the mixtures according to the invention is not critical.
  • the mixtures can therefore contain one or more further components in order to optimize various properties.
  • the observed effect on the response times and the threshold voltage is generally greater the higher the total concentration of compounds of the formulas I to XVIII.
  • a favorable synergistic effect with the compounds of formula I leads to particularly advantageous properties.
  • Mixtures containing compounds of formula I and formula IVa in particular are notable for their low threshold voltages.
  • the construction of the MFK display according to the invention from polarizers, electrode base plates and electrodes with surface treatment corresponds to the design customary for such displays.
  • the concept of conventional construction is broad here and includes all of them Modifications and modifications of the MFK display, in particular also matrix display elements based on poly-Si TFT or MIM.
  • liquid crystal mixtures which can be used according to the invention are prepared in a manner which is conventional per se.
  • the desired amount of the components used in smaller amounts is dissolved in the components which make up the main constituent, advantageously at elevated temperature.
  • solutions of the components in an organic solvent e.g. in acetone, chloroform or methanol and to remove the solvent after thorough mixing, for example by distillation.
  • the dielectrics can also contain further additives known to the person skilled in the art and described in the literature. For example, 0-15% pleochroic dyes or chiral dopants can be added.
  • V-, 0 denotes the voltage for 10% transmission (viewing direction perpendicular to the plate surface).
  • t on denotes the switch-on time and t off the switch-off time for an operating voltage corresponding to 2.5 times the value of V 10 .
  • ⁇ n denotes the optical anisotropy and n 0 the refractive index.
  • Table C lists possible dopants which are generally added to the mixtures according to the invention.
  • particularly preferred mixtures contain one, two, three, four, five or more compounds from Table B.

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

L'invention concerne un milieu à cristaux liquides à base d'un mélange de composés polaires à anisotropie diélectrique positive, caractérisé en ce qu'il contient un ou plusieurs composés de formule générale (I), dans laquelle R?1, A, L1, L2, L3, L4, L5, L6, Z1, Z2¿, X, v et u ont les significations indiquées dans la revendication 1.
PCT/EP2001/010901 2000-12-07 2001-09-20 Milieu a cristaux liquides WO2002046329A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US10/433,002 US7078079B2 (en) 2000-12-07 2001-09-20 Liquid-crystalline medium
AU2001289901A AU2001289901A1 (en) 2000-12-07 2001-09-20 Liquid crystalline medium

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE2000160744 DE10060744B4 (de) 2000-12-07 2000-12-07 Flüssigkristallines Medium und seine Verwendung
DE10060744.6 2000-12-07
DE2001125706 DE10125706A1 (de) 2001-05-25 2001-05-25 Flüssigkristallines Medium
DE10125706.6 2001-05-25

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WO2002046329A1 true WO2002046329A1 (fr) 2002-06-13

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US (1) US7078079B2 (fr)
AU (1) AU2001289901A1 (fr)
WO (1) WO2002046329A1 (fr)

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EP1302523A1 (fr) 2001-10-12 2003-04-16 MERCK PATENT GmbH Milieu liquide cristallin
EP1352943A1 (fr) * 2002-04-12 2003-10-15 MERCK PATENT GmbH Milieu liquide cristallin et dispositif d'affichage électro-optique le contenant
US6916513B2 (en) * 2001-04-07 2005-07-12 Merck Patent Gmbh 2,4′-Substituted 6-cyclohexyl-trans-decalines
CN102559203A (zh) * 2010-11-29 2012-07-11 默克专利股份有限公司 液晶混合物
WO2014063817A1 (fr) * 2012-10-25 2014-05-01 Merck Patent Gmbh Milieu cristal liquide et écran électro-optique à cristaux liquides
TWI550073B (zh) * 2007-02-13 2016-09-21 馬克專利公司 液晶介質

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CN101580715B (zh) * 2009-05-13 2013-11-20 江苏和成显示科技股份有限公司 具有极低折射率的液晶组合物
US9441160B2 (en) * 2012-12-27 2016-09-13 Dic Corporation Fluorobiphenyl-containing composition
CN103254907B (zh) * 2013-04-23 2016-01-20 石家庄诚志永华显示材料有限公司 负介电各向异性液晶组合物

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DE10111572B4 (de) * 2000-03-23 2009-11-12 Merck Patent Gmbh Flüssigkristallines Medium und seine Verwendung
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DE19814550A1 (de) * 1998-04-01 1999-10-07 Merck Patent Gmbh Vinylen- und Ethylverbindungen
DE19961015A1 (de) * 1998-12-22 2000-09-21 Merck Patent Gmbh Flüssigkristallines Medium
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Cited By (18)

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Publication number Priority date Publication date Assignee Title
US6916513B2 (en) * 2001-04-07 2005-07-12 Merck Patent Gmbh 2,4′-Substituted 6-cyclohexyl-trans-decalines
EP1373175B1 (fr) * 2001-04-07 2009-07-08 MERCK PATENT GmbH 6-cyclohexyl-trans-decalines substituees aux positions 2,4'
EP1302523A1 (fr) 2001-10-12 2003-04-16 MERCK PATENT GmbH Milieu liquide cristallin
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